Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor–Acceptor Cyclopropanes

Abstract

Two different Lewis acids were used for developing [3+2] and [3+3] regioselective cycloaddition reactions of an azomethine imine with activated cyclopropanes. Scandium(III) triflate catalyzes a [3+2] cycloaddition reaction of the azomethine imine with cyclopropanes to form tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives in moderate yields. Complementary to this, a novel [3+3] cycloaddition reaction of the azomethine imine with activated cyclopropanes was developed by using EtAlCl₂ as a Lewis acid to form hexahydropyridazinone derivatives in high regioselectivity.

Key words

pyrazolidines - [3+2] cycloaddition - [3+3] cycloaddition - azomethine imines - donor–acceptor cyclopropanes

Publication History

Received: 18 March 2021

Accepted after revision: 10 May 2021

Accepted Manuscript online:
10 May 2021

Article published online:
10 June 2021

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